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Evelyne White was immediately attracted to Frank Ramirez’s
profile picture. “He was holding a camera in it. I remember
seeing that photo and thinking, he’s probably a creative type,”
she says. “There was something about it that said he was a little
bit extroverted.”

Blonde and girl-next-door pretty, White arranged to meet Ramirez
for coffee last March. Her intuitions about Ramirez were right.
Dark-haired, with an athletic build and a penchant for rope
bracelets, Ramirez was in the process of leaving his corporate
position for a job he could be passionate about.

On both sides, there was an instant click of connection, the
elusive but immediate understanding that “this person gets me.”
They talked for three hours. For White, who had exchanged emails
with dozens of people and had been on similar coffee sitdowns
with at least five of them, she knew she’d found someone special.
“I put more cards on the table with him in the first meeting than
I had with anybody else.”

Almost a year later, Ramirez and White see each other almost
every day. They have an easy, casual rapport and share an obvious
mutual respect. White is good at big picture thinking, while
Ramirez is a deeply knowledgeable technical guy.

Here’s the thing: They’re not dating. They never were. But as
with a romantic relationship, they are embarking on an
emotionally daring, unpredictable and often exhausting ride –
they're
starting a business together.

Startup mythology is rooted in dorm-room “meet cute” stories;
Matt Mullenweg teaming up with two fellow classmates as a
freshmen at the University of Houston to build WordPress; Kevin
Systrom and Mike Krieger meeting at Stanford and eventually
launching the photography sharing app Instagram.

The appeal of these founding stories is obvious -- it gives the
successful startup a romantic tinge. Like Romeo and Juliet,
perhaps Sergey Brin and Larry Page were fated to meet as and play
out their own intense (albeit very different) drama.

Jessica Alter, co-founder of FounderDating, an invite-only
matchmaking site for entrepreneurs looking to connect with each
other or an advisor, has no patience for those who hang
back, waiting for Romeo to find them. If you are serious about
starting a business, she feels, it’s your responsibility to seek
out that perfect partner. “It doesn’t make sense for you to say
‘Either I already know this person or someone else will just
introduce me,’” she says. “That's arcane. We don't need to do
that anymore."

The first time Bhavin Shah founded a company, the stars aligned;
he met his co-founder, Robert Hutter, the “natural way” (the two
had worked together years back, and remained in touch). Together,
they started a gaming company, Gazillion Entertainment.

The next time around, Shah didn’t have time to wait for that
perfect storm to brew again. “Some things happen through pure
serendipity, but as a second or third time entrepreneur you don’t
want to leave your life to serendipity,” Shah says. “Many
successful companies are founded by people who go out and crush
it because they didn’t wait for something fortuitous to happen to
them.”

There’s a disconnect, Shah feels, between the reality of how many
successful startups are formed and the romantic origin myths that
get all the attention. He founded Refresh, an iPhone app which creates
an “instant dossier” for everyone you meet by aggregating data
from their social media accounts, with Paul Tyma, co-founder he
met online through Alter’s co-founder dating site; he credits the
matchup with Refresh’s subsequent success -- the startup recently
raised 10 million in Series A funding.

Starting a company with someone who, when the going gets tough,
simply doesn't have that entrepreneurial itch can be devastating.
Dustin Williams found that out the hard way. He tried to start
his first company with a friend. They labored for months over
their product (a hardware and software package for small
businesses) until his co-founder's wife got pregnant and quit her
job. William's friend promptly went back to work, abandoning him
and their incomplete prototype.

The next time around was even worse. Williams teamed up with
another friend who had recently left a job at AutoDesk to start a company that
they hoped would provide low cost solutions for rendering 3-D
graphics. An experienced engineer, Williams spent nine months
building the prototype. The plan was that his co-founder, a
business development guy, would shop around their product once
Williams finished.

"He was a longtime friend of mine…'was' being the key word here,"
Williams says. "He actually contacted me the day before my
wedding, and told me that not only could he not make it, but he
couldn't come because he needed to start his new job." Williams
was stuck with a product he had been working on for months, with
no contacts and thus no way to access customers.

The venture, unsurprisingly, failed.

Despite the friction that often results from working with
friends, there still seems to be a stigma against co-founders who
have met online, i.e. the "unnatural way," as David Rusenko,
co-founder of the web-hosting service Weebly, recently put it.
(He met his co-founders the natural way, at college).

It could even be a deal breaker for investors. Rick Nathan, who
served as president and chair of Canada’s Venture Capital and
Private Equity Association from 2005 to 2012, says he wouldn't
invest in a startup team if the co-founders hadn't worked
together in some sort of previous capacity. It's impossible, he
says, for anyone to know how they will get along when thrust into
the intense, around the clock schedule that is required for
getting a business up and running. Rolling the dice with a
previously untested pair is too big a risk.

Alter, however, insists that aspiring entrepreneurs who turn to
websites like hers for help face little backlash from the
entrepreneurial community; certainly, they’re met with less
skepticism
than traditional online daters were for years. She does see
useful parallels between the two, however. While the internet
great at identifying attractive partners, it’s less successful at
the ‘getting to know you’ part of the process. “I think people
tend to think you read someone's profile, say you want to start a
company with them and then you just do it,” she says. “It never
works that way.” Like romantic relationships that start on the
internet, it’s ultimately about connecting offline.

“I think there’s definitely some initial reluctance when it comes
to finding a co-founder online,” says Shahab Kaviani, CEO of the
entrepreneurial matchmaking site CoFoundersLab, where
Evelyne White and Frank Ramirez first met. But he’s
confident that this hesitation will dissipate, much as it did
with online dating. “Twelve years ago there was a lot of stigma
against it, and now one in six marriages start online,” he says.
“I know lots of people who are like, 'Hey! I met my wife on
eHarmony!’ It’s not a big deal anymore.” He finds the obvious
analogy between co-founder and romantic relationships a useful
one; its skeleton is essentially the same, just with different
appendages. “Instead of caring whether you smoke or not, I care
about the corporate culture you’re trying to create. Instead of
caring about how many kids you're interested in having, it's
about: do you want to make it a lifestyle business are you trying
to build a big VC company?”

A central advantage to online dating is the comforting knowledge
that everyone (or almost everyone – sites like Ashley Madison excluded) is
available, and actively seeking a romantic partner. Out there in
the real world, it’s impossible to know if the cute guy in front
of you in line at Starbucks, or the girl ordering a beer next to
you at the bar, is already dating. Going online -- where people
(at least ostensibly) are single – strips away the need to sniff
out availability.

On Kaviani’s site, like on OKCupid, everyone is welcome and
there’s no sticker price, while Alter’s site aims to keep the
quality of all those involved very high. Like the controversial
dating site beautifulpeople.com
(“ugly people,” it’s founder
told Business Insider, “need not apply”), FounderDating has a
rigorous application process; candidates are asked to submit at
least one reference, and the acceptance rate is currently 34
percent. Alter maintains a delicate balance between applicants
gifted in business/product/design etc., and engineers. Engineers
are always in hot demand, so Alter ensures that they account for
roughly 50 percent of accepted applicants. A team of
entrepreneurs screen to weed out anyone who is not serious about
starting a business (the initiation fee helps with this, too);
individuals who are at the stage of simply dreaming about giving
up their day job need not apply. “Because we screen, no one in
our network is hard up for a job. They have a LinkedIn inbox full
of jobs and recruiter requests. We're not a job network.”

For Shah, co-founder of Refresh, this was a major upside. Before
he joined Alter's site, he turned to his own network to test out
potential co-founders. “I talked to some fantastic people. They’d
get really excited, and then there first question to me would be:
‘OK, so what’s my salary going to be?” Shah says, incredulous
still. “And I’m like, ‘Gosh, we’re having this conversation this
early?’ Starting a company takes a lot of personal risk, both
professionally and financially. There are good days and bad days
for every company. The last thing you want is someone who can’t
really handle that and wants off the ship.”